胞嘧啶核苷键联卟啉的合成及其与牛血清白蛋白的相互作用

高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (9): 1724.

胞嘧啶核苷键联卟啉的合成及其与牛血清白蛋白的相互作用

江国防¹, 高峰¹, 张满生², 刘畅¹, 郭灿城¹

1. 化学生物传感与计量学国家重点实验室, 湖南大学化学化工学院, 长沙 410082;
2. 湖南公安高等专科学校, 长沙 410138

收稿日期:2008-12-11 出版日期:2009-09-10 发布日期:2009-09-10
通讯作者: 江国防, 男, 博士, 教授, 主要从事金属卟啉合成与仿生催化研究. E-mail: guofangjiang@yahoo.com.cn
基金资助:
国家自然科学基金(批准号: 20502005)、湖南省重点科技项目(批准号: 2008GK2023)和湖南大学重点基金(批准号: 521101787)资助.

Synthesis of Cytidine-bonded Porphyrins and Their Interaction with Bovine Serum Albumin

JIANG Guo-Fang^1*, GAO Feng¹, ZHANG Man-Sheng², LIU Chang¹, GUO Can-Cheng¹

1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China;
2. Hunan Public Security College, Changsha 410138, China

Received:2008-12-11 Online:2009-09-10 Published:2009-09-10
Contact: JIANG Guo-Fang. E-mail: guofangjiang@yahoo.com.cn
Supported by:
国家自然科学基金(批准号: 20502005)、湖南省重点科技项目(批准号: 2008GK2023)和湖南大学重点基金(批准号: 521101787)资助.

摘要/Abstract

摘要：

基于卟啉化合物的光敏性和对肿瘤细胞有特殊的亲和力以及核苷类化合物的抗肿瘤及抗癌活性, 设计合成了胞嘧啶核苷卟啉化合物6和8, 其结构由¹H NMR, IR, UV-Vis, MS 和元素分析表征. 同时, 利用荧光光谱考察了上述核苷卟啉与牛血清白蛋白(BSA)的相互作用, 结果表明它们对BSA荧光有较强的静态猝灭作用.

关键词: 胞嘧啶; 卟啉; 牛血清白蛋白; 荧光光谱

Abstract:

Cytidine-bonded porphyrins 6 and 8 were designed and synthesized on the basis of porphyrin′s photosensitivity, special affinity for tumor cells, nucleosides′ antitumor and anticancer activities. Molecular structures of all synthesized compounds were characterized by ¹H NMR, IR, UV-Vis, MS and elemental analysis. The interaction between cytidine-bonded porphyrins 6, 8 and bovine serum albumin(BSA) was investigated by fluorescence spectrum. The results show that the novel cytidine-bonded porphyrins 6 and 8 own a powerful ability of quenching the fluorescence of BSA via static quenching.

Key words: Cytidine; Porphyrin; Bovine serum albumin; Fluorescence spectrum

TrendMD:

江国防, 高峰, 张满生, 刘畅, 郭灿城. 胞嘧啶核苷键联卟啉的合成及其与牛血清白蛋白的相互作用. 高等学校化学学报, 2009, 30(9): 1724.

JIANG Guo-Fang*, GAO Feng, ZHANG Man-Sheng, LIU Chang, GUO Can-Cheng. Synthesis of Cytidine-bonded Porphyrins and Their Interaction with Bovine Serum Albumin. Chem. J. Chinese Universities, 2009, 30(9): 1724.

参考文献

[1]Nakagawa K., Kitagawa T., Sadaoka Y.. Sens. Actuators, B[J], 1998, 52: 10—14
[2]Lau R. L. C., Jiang J., Ng D. K. P., et al.. J. Am. Soc. Mass. Spectrom.[J], 1997, 8: 161—169
[3]Sternberg E. D., Dolphin D., Brucker C.. Tetrahedron[J], 1998, 54(17): 4151—4202
[4]Ford K. G., Pear L. H., Neidle S.. Nucleic Acids Res.[J] 1987, 15: 6553—6562
[5]Eaton S. S., Fishwild D. M., Eaton D. M.. Inorg. Chem.[J], 1978, 17: 1542—1545
[6]Detty M. R., Gibson S. L., Wagner S. J.. J. Med. Chem.[J], 2004, 47: 3897—3915
[7]Ayub J., David D.. Chem. Rev.[J], 1997, 97: 2287—2340
[8]Nyman E. S., Hynninen P. H.. J. Photochem. Photobiol., B[J], 2004, 73: 1—28
[9]Yasuhisa K., Yusuke K., Takuji H., et al.. J. Am. Chem. Soc.[J], 1995, 117: 10950—10958
[10]Mialocq J. C., Giaunotti C., Mailand P., et al.. Chem. Phys. Lett.[J], 1984, 112: 87—93
[11]Roberts W. K., Dekker C. A.. J. Org. Chem.[J], 1967, 32: 816—817
[12]Kikugawa K., Ichino M.. Tetrahedron Lett.[J], 1970, 11: 867—870
[13]Hamamura E. K., Prystasz M., Verheyden J. P. H., et al.. J. Med. Chem.[J], 1976, 19(5): 654—662
[14]Cartor A. J., Ballard S. A., Naylor A. M.. J. Urol.[J], 1998, 160: 242—246
[15]Marcuccio S. M., Elmes B. C., Holan G., et al.. Nucleosides & Nucleotides[J], 1992, 11: 1695—1701
[16]Kang Y. J., Raymond J. H., Andrew J. W., et al.. Bioorg. Med. Chem.[J], 2000, 8: 2501—2509
[17]HUANG Su-Qiu(黄素秋), SUN Lu-Ming(孙鲁名), YE Jiao(叶峤). Chem. J. Chinese Universities(高等学校化学学报)[J], 1983, 4(2): 381—384
[18]ZHU Keng(朱铿), TONG Shen-Yang(童沈阳). Acta Chim. Sinica(化学学报)[J], 1997, 55: 405—410
[19]Lepecq J. B., Paoletti C.. Anal. Biochem.[J], 1966, 17: 100—107
[20]Prasad A. R. S., Luduena R. F., Horowitz M. P.. Biochemistry[J], 1986, 25: 3536—3540
[21]JIA Tao(贾涛), WANG Kai(王凯), BAO Xiao-Ping(鲍小平), et al.. Chem.J. Chinese Universities(高等学校化学学报)[J],2004, 25(9): 1604—1607